Chi-Town is a Bike Town

Sitting atop two wheels is one of the best ways to see Chicago, often rated one of the best places for biking in the country. So now that the Ambassador has complimentary bikes for guests to use during warmer months, we suggest taking out one for a few hours and riding around the Gold Coast (the gorgeous historic neighborhood the Ambassador is located in) or up and down the lakeshore path (a must-visit spot while you’re in Chicago).

Or, if you’re feeling a little more on the adventurous side, pedal away in one of the many biking events held throughout the city. Here are a few not to miss:

History of Cycling in Chicago Tour

Chicago’s connection to cycling goes way back. And while this city has tons of different tours you can take—from the architectural boat ride down the Chicago River to a view inside Frank Lloyd Wright’s Robie House in Hyde Park—this is the only one designed with bikers in mind. Ever heard of the “Famous Race to Pullman”? You will after taking this tour, which happens on May 20 and lasts all day. You’ll be joined by cyclists riding antique bikes and will pedal past places where major indoor and outdoor races used to be held, as well as some of the buildings where bicycles were manufactured.

Chicago’s connection to cycling goes way back. And while this city has tons of different tours you can take, this is the only one designed with bikers in mind.

Critical Mass

If you’ve never biked through city streets without worrying about cars, this event is going to blow your mind. The last Friday of each month, throngs of bikers meet up at Daley Plaza around 5:30 or 6 pm to bike together through the city. The goal: Remind people that bikers have a right to the road. It’s all-inclusive and has been described as a “rolling celebration,” so don’t worry about whether or not you’ll be welcome.

Bike the Drive

Each year at the end of May, Lake Shore Drive (the highway that runs along the coast of Lake Michigan) gets shut down to cars and taken over by cyclists. This year’s two-wheel takeover happens on Sunday, May 27. The car-free stretch of LSD goes from Bryn Mawr on the north to the Museum of Science and Industry on the south. Do the whole thing up and back and you’ll be pedaling for 30 miles, but you can choose to go for as long or as short as you’d like. Just remember to start early (cars are only banned for five hours, so you should get going by 7 am) and pre-register here.

Each year at the end of May, Lake Shore Drive gets shut down to cars and taken over by cyclists.

Naked Bike Ride

This is the 15th year in a row that people around the world strip down and start pedaling as a way to promote concepts like freedom from oil and positivity. Full nudity is “at your own risk,” (Chicago does have laws against indecent exposure, after all) but you can get creative with bathing suits, body paint, and fun costumes. This year’s ride happens on Saturday June 9 at sunset.